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CAS No.: | 1231929-97-7 |
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Name: | LY2835219 |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C27H32F2N8 |
Molecular Weight: | 506.601 |
Synonyms: | N-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-5-fluoro-4-(7-fluoro-2-methyl-3-propan-2-ylbenzimidazol-5-yl)pyrimidin-2-amine;2-Pyrimidinamine,N-[5-[(4-ethyl-1-piperazinyl)methyl]-2-pyridinyl]-5-fluoro-4-[4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl];LY2835219;[5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-[5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3H-benzoimidazol-5-yl)-pyrimidin-2-yl]-amine;Bemaciclib;CS-1230; |
Density: | 1.32±0.1 g/cm3(Predicted) |
Boiling Point: | 689.3±65.0 °C(Predicted) |
PSA: | 75.00000 |
LogP: | 4.88570 |
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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Stage #1: N-[5-(4-ethylpiperazine-1-yl-methyl)pyridine-2-yl]guanidine nitrate With sulfuric acid; sodium methylate In methanol; N,N-dimethyl-formamide at 30 - 35℃; for 2h; Stage #2: 6-(3-N,N-dimethylamino-2-fluoro-2-acrylketone-1-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzimidazole at 80 - 85℃; for 7h; | 90.8% |
With sodium hydroxide In butan-1-ol at 90 - 100℃; Inert atmosphere; | 73.1% |
5-((4-ethylpiperazin-1-yl)methyl)-6-methylpyridin-2-amine
6-bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 98 - 100℃; Inert atmosphere; | 82.85% |
4-ethylpiperazine
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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With formic acid; trimethyl orthoformate In acetonitrile at 80℃; for 16h; Reagent/catalyst; Leukardt-Wallach Amination; Sealed tube; | 74% |
5-((4-ethylpiperazin-1-yl)methyl)-6-methylpyridin-2-amine
6-(2-chloro-5-fluoropyrimidin-4-yl)-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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With potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In tert-Amyl alcohol at 100℃; for 19h; | 57.3% |
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 2h; Product distribution / selectivity; Inert atmosphere; | |
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 22.11 g |
4-fluoro-1-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-benzo[d]imidazole
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere 1.2: 5.5 h / 80 °C / Inert atmosphere 2.1: palladium dichloride; potassium carbonate / tert-Amyl alcohol / 18 h / 100 °C / Inert atmosphere 3.1: trimethyl orthoformate; formic acid / acetonitrile / 16 h / 80 °C / Sealed tube View Scheme | |
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 1 h / 80 - 84 °C / Inert atmosphere 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere View Scheme |
N-isopropylacetamide
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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Multi-step reaction with 5 steps 1: triethylamine; trichlorophosphate / toluene / 3 h / Reflux 2: potassium tert-butylate; N-Methylformamide / 70 - 75 °C / Large scale 3: tricyclohexylphosphine; potassium acetate; palladium diacetate / dimethyl sulfoxide / 1 h / 90 °C / Inert atmosphere 4: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 1 h / 80 - 84 °C / Inert atmosphere 5: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: trichlorophosphate; triethylamine / toluene / 10 °C / Reflux 2: potassium hydroxide / toluene; dimethyl sulfoxide / 30 °C / Reflux 3: potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 98 - 100 °C / Inert atmosphere View Scheme |
N-(4-bromo-2,6-difluorophenyl)-N'-isopropylacetamidine
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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Multi-step reaction with 4 steps 1: potassium tert-butylate; N-Methylformamide / 70 - 75 °C / Large scale 2: tricyclohexylphosphine; potassium acetate; palladium diacetate / dimethyl sulfoxide / 1 h / 90 °C / Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 1 h / 80 - 84 °C / Inert atmosphere 4: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere View Scheme |
6-bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: tricyclohexylphosphine; potassium acetate; palladium diacetate / dimethyl sulfoxide / 1 h / 90 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,2-dimethoxyethane / 1 h / 80 - 84 °C / Inert atmosphere 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere View Scheme |
4-ethylpiperazine
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / 20 - 30 °C / Large scale 2: ammonia / methanol / 40 - 75 °C 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere View Scheme |
6-bromonicotinaldehyde
N-(5-((4-ethyl-1-piperazinyl)methyl)-2-pyridinyl)-5-fluoro-4-(4-fluoro-2-methyl-1-(1-methylethyl)-1H-benzimidazol-6-yl)-2-pyrimidinamine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / 20 - 30 °C / Large scale 2: ammonia / methanol / 40 - 75 °C 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere View Scheme |